This article is a study of a transnational Chinese family whose members maintained contact between Southeast Asia and their native place in South China over the course of two generations. Their history illustrates the complex transnational and transregional interactions between Chinese communities in Southeast Asia and South China. Based upon approximately one hundred emigrants' remittance letters (qiaopi) from before 1949 as well as contemporary field research, the article shows how dynamic mechanisms within the transnational family structure and transnational communities enabled families to survive a difficult political and economic environment. The article provides a case study to reflect on the challenge posed by the transnational Chinese family to models of the ethnic nation-state and on the utility of transnationalism as the oretical formulation for the field of overseas Chinese studies.